For Bailey, the sharing economy means more than simply letting out his spare sofa bed. The 32-year-old interior and exterior designer manages a five-bedroom mansion in Clareville, in Sydney's northern beaches, owned by a friend and rented out for the hefty price of $990 a night through Airbnb.

The Airbnb experiment paid off. The house generates between $7000 and $8000 a week in rent, and up to $16,000 a week in the peak season. The property is booked 70 per cent of the time. If he rented out the property on a longer term, he would get only up to $4000 a week.

"With a permanent rental, you've got a security of a 12-month lease but with Airbnb you can see if it works for you or not and use the property on the weekend as a holiday home," says Bailey, who tells AFR Weekend he does not have a last name – confirmed by a quick look at his driver's licence.

Tass Schmidt rents out a luxury farm property in Jamberoo through Airbnb.
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Airbnb is now valued at about $US25 billion ($34.7 billion). Having swiftly moved into the mid-market with listings rivalling major hotel chains, it's now flirting with the luxury end. But numbers are so far small: just 200 of its 10,000 listings in Sydney go for more than $1000 a night. In Melbourne, it's just 30 out of 9000 listings.

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Tass Schmidt, who manages a luxury, $800-a-night five bedroom farm property in Jamberoo from an on-site office through Airbnb, said high end customers now expected better service. "We're starting to offer the kind of services guests would expect in a five star hotel. It might not be at that level, but it's the intention," she says.

Schmidt says as more luxurious properties emerge on platforms like Airbnb it opened up more opportunities for property managers. "The owners are usually so wealthy and they usually want a bit of return for their property and they don't want to be on call."

Luxury travellers still reluctant

Incumbents of luxury tourism industry are keen to preserve their patch. Alissa Hildebrand, chief executive of travel concierge company Valet Private, says high-end customers are reluctant to use Airbnb.

Bailey chilling out in the Clareville mansion.
Janie Barrett

"You really don't know what you're getting. It's a big risk for luxury travellers to pay a significant amount of money and paying it upfront with no real guarantee," she says.

She thinks those who list their luxury properties on Airbnb need to refine their offering.

"If they want to target the luxury market, they need to get small things right like fire protection, provide 100 per cent guarantee for their properties, and perhaps have an external agency managing the property for them," she says.

Other sharing economy-style platforms hope to keep the high end to themselves. Onefinestay inspects all the properties before listing them on its website and provides its own concierge and cleaning services. It says only one in 10 properties are accepted for listing, keeping its well-heeled clients away from riff-raff. The platform only covers homes in London, Los Angeles, New York or Paris, with no plans to expand into Australia.